Patent GB-427588-A (GB)
Title: A method for the production of hydrogenation products of the follicle hormone
IPC: C07J75/00
Filed: 1934-04-12
Abstract: Solutions of follicle hormone (C18H22O2), or of crude products containing, in addition, less saturated hormones (C18H20O2 and C18H18O2), are treated with hydrogen under pressure in presence of hydrogenation catalysts in such manner as to saturate the benzene nucleus and to convert the keto group to the corresponding secondary alcohol group.  According to one example, a solution of the hormone in 10 per cent potassium hydroxide is hydrogenated at 100 atmospheres and 160 DEG  C. using a previously reduced nickel-copper catalyst, the alkaline solution is extracted with ether and the ethereal solution evaporated to dryness to yield a glass-like residue of formula C18H30O2 which may be distilled in a high vacuum to yield several crystalline fractions all of which are active in the capon comb test.  The alkaline mother liquors after the extraction with ether yield, on acidification, the dihydrofollicle hormone. According to a second example, a solution of the hormone in cyclohexanol is hydrogenated at 60 to 70 atmospheres and 170 DEG  C. in presence of reduced nickel catalyst. The cyclohexanol is removed by vacuum distillation, the residue taken up in ether, and the ether solution extracted with aqueous alkali solution to remove any unchanged starting material.  The Specification as open to inspection under Sect. 91 refers also to catalytic hydrogenation in such manner that the benzene nucleus is hydrogenated but the keto group remains intact.  This subject-matter does not appear in the Specification as accepted.ALSO:Solutions of follicle hormone (C18H22O2), or of crude products containing, in addition, less saturated hormones (C18H20O2 and C18H18O2), are treated with hydrogen under pressure in presence of hydrogenation catalysts in such manner as to saturate the benzene nucleus and to convert the keto group to the corresponding secondary alcohol group.  According to one example, a solution of the hormone in 10 per cent potassium hydroxide is hydrogenated at 100 atmospheres and 160 DEG  C. using a previously reduced nickel-copper catalyst, the alkaline solution is extracted with ether and the ethereal solution evaporated to dryness to yield a glass-like residue of formula C18H30O2 which may be distilled in a high vacuum to yield several crystalline fractions all of which are active in the capon comb test.  The alkaline mother liquors after the extraction with ether yield, on acidification, the dihydrofollicle hormone. According to a second example, a solution of the hormone in cyclohexanol is hydrogenated at 60 to 70 atmospheres and 170 DEG  C. in presence of reduced nickel catalyst. The cyclohexanol is removed by vacuum distillation, the residue taken up in ether, and the ether solution extracted with aqueous alkali solution to remove any unchanged starting material.  The Specification as open to inspection under Sect. 91 refers also to catalytic hydrogenation in such manner that the benzene nucleus is hydrogenated but the keto group remains intact.  This subject-matter does not appear in the Specification as accepted.